Following his release from Arkham Asylum by Ra's al Ghul, Schiff came under the "employment" of the Joker, who used him as a calling card in his scheme to kill Gotham City's mayor Anthony Garcia during the funeral of Commissioner Gillian B. Loeb, disguised as an Honor Guards. When Police Lt. Jim Gordon foiled the assassination attempt by taking the bullets instead, the funeral went into a frenzy as the Joker and his gang escaped into it, leaving Schiff behind when he was shot in the leg. Harvey Dent saw Schiff's name tag, which read "Officer Rachel Dawes" and kidnapped him for information on what was going to happen to real Rachel.

Batman interceded, fully believing that Dent may kill Schiff if he flipped a coin in favor of it, but didn't realize the coin was a misprint, and had two head sides. Dent used it only to scare a confession from Schiff, but wasn't planning to actually murder him. Batman informed him that Schiff was a paranoid schizophrenic, and probably couldn't reveal anything.